A Cupcake For Your Heartache

by Dark Chocolate

Rating: mature
Tags: Pinkie Pie, Sex, Human, Sad, Romance, Drama, Original Character, Equestria Girls
Length: 3857

My first time couldn't have been with a sweeter girl. She knew how to pull on my heart strings, as well as how to pull on any other part of me. Two hours before my flight, and the conversation between us in her car, takes a surprising turn.

Nikky Fabulous #3, the sequel to The Fluttershy Effect
Three years ago I had met a wonderful, silly girl as sweet as the treats she often craved. Our freshmen year felt like an entire lifetime. My only regret, was not doing more with her when I had the time.

Authors note:
The first chapter is three years before Wrestling A Rainbow

Published 2016-05-06 22:00:01 UTC
Last updated 2016-05-06 22:00:01 UTC

First Time In The Oven

Pinkie Pie pulls into a parking lot. I sit in the passenger seat with my arms crossed, trying to cover up my excessive mass. We sit silently, knowing this will be the last time we will talk face to face for quite some time. We had two hours until we had to get on the highway to the airport, so I could go live with my uncle.

Pinkie and I had been close since the first day we met. I was always up for trying her cooking, even though she hadn’t quite mastered it yet. She may have been part of the reason I was 400 pounds now, but it was honestly my own bad habits.

She runs her fingers along the steering wheel, both of us dying for something to break the ice. I drum my fingers on my arm, wanting something to say, but having nothing. I started wondering why she was being quiet as well. I inhale as much as I can, hoping to also get some courage from the air, “I’ll..miss your cookies…”

Her head snaps towards me, and a big smile crosses her face. She gently bats my arm, “I’ll miss my favorite customer…” Her light blue eyes make me shiver on the inside. Her gaze reflects the most compassion and friendship anyone had ever shown me. We look into each others eyes and start giggling. She looks down at her steering wheel again, "This sounds like the beginning of a really bad porno..." she says while gently laughing.

Pinkie and her friends were literally the only girls who hadn’t made fun of me for my weight. I had first met Pinkie as she sat sadly outside Canterlot high, with a container of burnt cookies. Not being picky, I asked to taste one. Despite them being horrendous, I ate them all. After that, we went back to her house and perfected the recipe. By perfected, I mean they no longer made me gag. No matter how bad they were, I kept encouraging her, offering advice, being her taste tester, and eventually she nailed it.

And now we were about to say goodbye for a long long time, and yet I'm still a coward. Every time I look at her for longer than a few seconds, I shiver. I told her they were stomach aches. Ya it was my stomach alright, and it was full of annoying butterflies. I rub my hands together, "Thanks for being my friend."

She looks back to me again, her eyes are engulfed with intimacy, "You don't have to thank me! I was happy you were my friend too!"
I look down sadly "I know, but I also know I can be a handful...well several handfuls but you know what I mean." I say, while grabbing a hold of my stomach and jiggling it up and down jokingly. I made a lot of jokes to compensate for my insecurities. Pinkie had always encouraged me to stop doing it, but it was another bad habit. She chuckles and shakes her head.

"And don't forget Pinkie, you'll always be the cupcake I won't eat...well unless we're in a desperate survival situation, in which case all bets are off." She hunches over her steering wheel laughing. She bonks the horn with her head a few times on accident, which makes us both laugh even harder. I knew my joke wasn't all that funny, but it was more nerves than anything that got us laughing.

After a few minutes of us laughing the tension out, we settle down and go back to being miserable.
I look out the car window, "You know, I never thanked you for being one of the few girls who weren't ashamed to see me in public."
Her lip trembles a bit, but she keeps her head hanged.

She sniffles "Well thank you for being one of the few people who gave me a chance."
She pauses for a minute then continues, "You know...I never cared about your weight."
My head snaps to her, "R...really?"
She shrugs, "I mean...ya there's health concerns but, i mean it's not like it's a dealbreaker to me." She gazes out the window, leaving that tiny hint in the air. What did she mean by not a dealbreaker?! Was she hinting at something? I knew she was...she said it intentionally but...what do I do with that?! Why didn't she say this sooner?! I'm about to leave, and she drops this in my lap?

She slowly looks over at me. I'm shaking so bad you'd think I was going into shock. I rub my hands way too hard, but I don't notice. They begin to grow red with friction. My cheeks are the inside of a volcano, and my thoughts are a trainwreck...inside a volcano...being carpet bombed. I want to say anything, anything at all.

Her lips gradually form an amused smile, "Just...say what's on your mind..."
I stare at her like a deer in headlights, "Y...you're...pretty." My left eye twitches. That was all I had. I just wanted to say something nice to her.
She pokes my arm a few times "Nice pickup line Edgar Allen Poe." We stare into eachother for what feels like forever, and nothing else mattered to me. I would have given anything for her to see my feelings in my eyes. Neither of us are smiling, just enjoying the moment. Was this real? Was this actually happening?

She reaches down and unbuckles her belt. She slides over the shifter, and sits in my lap. She rests her head against my chest, closes her eyes, and looks perfectly at peace. My legs could have been on fire and I still wouldn't have moved. Nothing was going to ruin this moment. Even if something did, it would live on in my memory as one of the happiest days of my life. My arms instinctively lose around her. I nuzzle the top of her adorable head with mine. This was going to be the closest I was going to get to dating her. Everything was perfect...right up until I started getting an erection.

I begin to panic. Eventually it was going to poke her bottom and there was no greater horror. We were having a perfectly romantic time and here I was about to wreck it. I can't resist the feel of her warm, smooth cheeks on my leg. I feel her breathing against my chest, her gentle frame resting against mine. She giggles a bit, "Your heart is going like a jack hammer." All she hears from me is nervous gasping. She exhales with relaxation, "You're so warm and comfy." She digs into me deeper. I bit my lip as I can now see down her shirt a bit. I desperately try to divert my eyes but...I've wanted her for so long. Every giggle, every time we had accidentally brushed arms, every nice thing she had ever said to me, they were always on my mind.

What I felt for her was beyond anything I had experienced before. Was this love? There was nothing I wasn't willing to do to put a smile on her face. She was everything to me. Now was my darkest hour. The totality of everything we had been through together was about to go down the drain. My pants were too tight and I could feel myself slowly slipping from it's housing and moving upwards. Any minute now this paradise would fade from existence.

Pinkie's eyes open suddenly, "Mmmmmm, well someone's glad to see me..." she says seductively.
And just like that, it was over. I had lost my best friend as the gate's of hell themselves opened- wait what did she say?
She looks up at me, her eyes narrowed, her mouth curled up in a grin. I feel myself bob up once. She lets out a quiet but surprised squeal.
She reaches up with her left hand and rests it on my cheek. With that mischievous smile, she pulls me in and kisses me. A few seconds pass, as she keeps her lips on mine. I kiss her back out of reflex but I'm unable to comprehend anything.

I wrap her in a tight hug, as we lock lips a few more times. It feels as if a stream of passion is flowing from me. I had countless fantasies like this, but it was actually happening. I'm caught up in a storm of passion and the inconceivable idea that she felt the same way. We stop kissing and she throws her arms around my neck, hugging me with the same amount of passion that I showed her. She rubs her cheek against mine a few times. I close my eyes as we embrace, letting every ounce of insecurity leave me. All I can feel is the warmth of her body, accompanied by that familiar smell of frosting from her hair.

I feel her twitch a few times, as my warm breath surrounds her ear. Her mouth trembles in a delicate smile against my cheek. I start kissing her ear, and her hands clamp a bit harder on my shoulders. I gradually drag my fingertips down the middle of her back. She presses her chest into me, as quiet moans escape her mouth. She starts kissing my neck, and gently massages my meat with her knee. I quiver and faintly moan in her ear.

She leans in close. I hear her lick her lips before she whispers to me.
"You can do better than that right?" her seductive words pull something out of me. My hands and my head start shaking. I feel my jaw vibrate as every last fantasy I had ever had about plays infront of me like my own personal dirty movie. I can't deny what I've been craving all these months.

I devour her neck as if I hadn't eaten in months. I clamp my right hand on her rear with a firm smack. I grab her cheek hard enough that I could lift her up if I wanted. She lets out a loud pleasurable moan right into my eardrum. I aggressively rummage up her back with my left hand, unable to get my fill of her skin. She holds onto my neck for dear life, allowing me to do as I please.

My left hand slides up to her bra and unhooks it after a few tries. My mouth moves from her neck, to right under her jaw. She leans her head back, but leaving her chest right where it is, almost as if she was baiting me. I wrench her shirt and bra up in one motion. I'm taken aback by the sight of her perfect perky breasts gently bobbing with her panting. Her delicious purple nipples call to me. I take one in my mouth and suck hard. She lets out a loud moan, and pulls my head harder into her breast.

I pull my head back, still keeping suction on her tit. She braces herself with her left arm against the dash, still keeping her right on my neck. Her chest rocks forward a bit. I release the pressure on her nipple, as I caress its shape with my tongue. I stop with her tit, grab both breasts, and massage my face with them. Her panting has made the windows fog. She pushes me off her, back into the seat. She lunges forward, slamming her tongue into mine.

Her hot, slippery tongue does its best to wrap around mine. My hands go back to that delicious booty of hers. I get as many firm, hungry gropes in as I can, enjoying each luscious squeeze. I run my hands along her perfect curves. My hands almost tremble from the excitement. My hands go up and down that gorgeous round ass. I give it slow, tender squeezes, being completely intoxicated by the feel of her soft body against me.

She takes her tongue out of my mouth and looks into my eyes for a few brief seconds. We enjoy the feel of eachothers hot breath on our faces. She has an almost satiated smile . Her cheeks are flushed, but I'm sure mine as as well. My entire face burned. I didn't care if I was being rude anymore, all I knew was desire. Those silly insecurities had left me. She traces the left side of my face with her fingertips, almost unable to believe I was the same person.

She brushes some of her hair back, "So um...do we wanna take this to the backseat?" I manage a nod. My hard, throbbing meat interferes with any words that pop into my mind. She glances down and strokes it through my pants a few times. She opens the passenger door and very slowly slides off my lap, making sure not to break eye contact. She stands outside the car; watching me.

I swing my legs over, and as I stand, she makes sure I'm brushing up against her the entire time. She takes my hand and leads me to the rear door. As she opens it and bends over to get in, I feel my hand lunge forward and give her a loud spank. She let out a loud excited squeal before turning around and pulling me in by my shirt collar. I was still in shock at my own behavior. It was something oddly primitive. Part of me just knew what to do. Too many dirty movies perhaps, but regardless for the first time in my life, I was enjoying myself.

We constantly kiss as she scurries backwards into the seat, not taking her hands off my shirt collar. She leans against the door as I start running my hands up and down her legs, giving her inner thighs several compassionate kisses. She watches me eagerly, shaking briefly with each tender stroke of my finger. I take her panties in my fingers and slide them off, still kissing her legs as I remove them.

I place my hands on her hips, making my way towards her opening. I slide my tongue along her skin, trying to draw out as much anticipation as I can. Her panting gets heavier and heavier. She grabs my hair and fores my face into her. She wraps her legs around my head as I massage every moist bump. I move her clit back and forth with my tongue. She lets out repeated loud cries of pleasure over and over. I reach up under her shirt, and grope her breasts over and over. She places her hands on top of mine. With her eyes closed, her head thrashes left and right.

She rocks her pelvis left and right, as I continue exploring her clit with my tongue. My hands travel from her chest, down to that delicious ass of hers. I grab both cheeks, shoving her vag into my mouth even harder. I continually run my hands down her cheeks to her thighs, then back again. She braces herself with one arm, and uses her free hand to shove my face in harder. Her cries quickly get louder and louder. I stick my tongue inside her opening, wiggling around as much as I can. She grabs my hair with all her might as she takes in one last breath before convulsing.

I raise my head, my tongue is sore and so is my neck; not a single part of me cares. I had been dying for her touch longer than I could remember. I'm surprised when she grabs my shirt and pulls me in for a deep passionate kiss. We press our lips together over and over, not bothering with small talk. She finally pulls away from me, almost acting drunk with her last orgasm. She uses her index finger to move some hair from my forhead. After a few seconds, she grins at me, "Ok...your turn honey." she follows it up with a small giggle.

I sit in the backseat, doing my best to relax. She kisses me a few times, stroking my hard meat with her tiny hands. I do my best to kiss her, but my mouth stutters a few times. I let out a few moans, not used to having someone else play with it. She lets go, sticks her hand down the front of my sweats, and pulls it out. She strokes it a few more times while kissing me. She glances down and her eyes grow wide.
I see an impressed grin on her face, "Well...aren't you gifted."

She moves up her small hands gently taking my shaft in her grasp, slowly stroking up to the tip of my cock and sliding back down in a swift soft motion. Her fingertips delicately trace down the sides, before she leans in close, running her tongue across the tip of my cock in small circles, blowing a soft cool stream of air across the tip afterwards, before kissing down the shaft, nice and slow.

I groan with pleasure, as my eyes narrow in both shock and ecstasy. My meat bounces a few times, eager to feel the insides of Pinkie's warm mouth against it. Every part of me wants to shove it into her mouth, but somehow I resist. Her hungry eyes drive me wild, full of anticipation for the meal about to come.

Her eyes sparkle softly as they lift up locking on mine. She softly kiss down to the base of my cock, her full soft lips kiss across my sack slowly. Her warm tongue flicking each ball teasingly, she giggles softly as her tongue gently traces up every inch of my meat; swollen and ready. She wraps full pouting lips around my head, softly bobbing down, sliding inch after inch of hard, throbbing meat down her tight, warm throat.

I convulse a bit, the tip of my meat screams at me in response to her voracious assault. I stroke the back of her head, enjoying the feeling of having my cock sucked so enthusiastically. She scoots forward, enjoying every inch of my cock she can get her mouth on. My right hand reaches forward, down her shirt, and firmly massages a nice large breast.

She moans softly, voice sweet and wanting my manhood. She slowly slides off my shaft, giggling as she slowly lifts up her whit shirt, showing me her firm soft breasts held by a silk black bra, with a smirk she removes her bra completely; flesh falling free ,perky ,soft and bouncing. She blinks long lashes, bobbing down upon my shaft once again, wrapping lips firmly around the head, sucking slowly and deeply, inch after inch she slides it down her throat. Warm soft tongue gently massages down the shaft, lifting upward as she flicks the head teasingly with her tongue. She locks eyes with me as I moan.

My head shakes uncontrollably. I can't stand the sight and feel of her dragging her tongue up and down my meat. I can barely speak through my panting, "P..Pinkie...I...I'm coming..." She looks up at me with that dirty smile she's so good with. She gives my head one last slow, powerful suck, before starting at the base of my shaft and dragging her tongue upwards. Before she gets to the top again, I can't help it. I do my best to hold back, but cum begins to flow out like a water fountain. She doesn't seem to find, as she keeps slowly licking upwards, despite the cum pouring across her fingers.

She gets half way up as even more begins to ooze out. She doesn't taker her eyes off me. I watch in shock as she gets back to the head, and still keeps sucking on it. My eyes roll back as she traces very last solid curve of my head with her tongue, as if enjoying rare candy. My face goes red as the sensitivity is too much. She casually licks off every drop from both my cock and her fingers.

She leans back into the seat. We both sit there for a few minutes, before she scoots over and rests her head on my shoulder. A large portion of her fluffy pink hair falls infront of my face. I don't mind. Somewhere deep inside, the braver part of me has found his way out. I lean over and stare at her until she notices and look back at me. That cute gentle smile cuts right through me. I place my hand on her right cheek, and pull her in for my own dreamy kiss. After our lips touch, a wave of warmth washes over me.

I pull away, "Ho...how long have you had...feelings for me?"
She sets her head on my chest and sighs happily, "I dono...like...I guess when I started cooking better. Like the moment I realized you were always there for me, and encouraged me when no one else did...I dono I guess I just started...really getting to know you."
I may have nodded in understanding, but I was baffled it had been going on this long. Part of me always felt connected to her, and I had countless fantasies of us dating.

Our time together is crucified when I glance at the clock. We had to get going immediately. She sees my grim expression and notices the time too. Without saying anything, she puts her bra back on, and we get back in the front. The drive is quiet, and a deep stabbing feeling in my gut appears as we get closer and closer to the airport.

With my ticket in hand, I stand a few meters away from the line for security. The color drains from my face as I gaze at Pinkie's depressed face one last time. I feel a few tears make their way down my cheek. Pinkie's face lights up slightly, "I thought girls were suppose to be the ones crying..." I sniffle, "To hell with stereotypes. I'm going to miss you every second I'm out there." My shoulders start shaking up and down as I slowly loose it. I clench my eyes shut, trying to control myself. I couldn't deny how lonely I was. Every thought of every couple I had been envious of, played in my mind. And now I was giving up the first girl who ever shared my feelings.

I knew I had to go, I knew it was for the best. I knew my uncle was going to break me out of my terrified shell, and teach me everything i ever needed to know. A firm, warm hug brings me out of it. I wrap my arms around Pinkie, doing my best not to squeeze the air out of her. My eyes instinctively glance at the clock. We let go. She pulls out a handkerchief and wipes my eyes and cheeks. She glances down at it. It's pink with a few blue balloons on it. She stuffs it in my pocket, "I'll never make anything as sweet as you Nikky..."

With that, I check my bags through security. Just like that, she was gone.